Blessed is the man whose strength is in You,
Whose heart is set on pilgrimage.

Psalm 84:5

For 7 years I have made these pilgrim pies but I honestly doubt the pilgrims ever experienced such a delightful delicacy! It has become somewhat of an unspoken tradition for me to make my first batch in the first week of October(can any one believe it is already October?!). If I don’t make these pies as soon as the 1st of October twirls around, I am reminded by 1/2 dozen kidlettes that, “it is officially Pilgrim Pie Season”!

Original Recipe Yield 12-15 “pies”


  • 2 eggs
  • 2 cups brown sugar
  • 1 cup vegetable oil
  • 1 tsp vanilla
  • 1 (15oz) can Pureed Pumpkin or 2 cups freshly pureed pumpkin(I used freshly pureed)
  • 3 cups flour
  • 1tbs pumpkin pie spice
  • 1 tsp baking soda
  • 1 tsp baking powder
  • 1 tsp salt
  • 4 oz cream cheese – softened
  • 1/2 cup butter – softened
  • 2tsp vanilla
  • 4-5 cups powder sugar


  1. Heat oven to 350 degrees .
  2. Beat eggs, sugar, oil, vanilla, and pumpkin  in large bowl. Add flour, pumpkin pie spice, soda, powder, and salt until well combine.
  3. Using an ice cream scoop(my favorite kitchen tool) or large spoon, spoon 1/4 cup dallops onto ungreased cookie sheet 1 1/2 inches apart. Bake for 11-14 minutes or until bottoms are golden. Let cool on tray for 5 minutes then remove from tray and let  cool completely on parchment.
  4. Prepare filling. Combine all filling ingredients and blend on high speed until smooth and fluffy!
  5. Pipe filling onto 1 cookie and top with the second cookie. Continue with remaining cookies and Enjoy!